When you’re hosting the MTV Movie Awards and promise viewers “The Biggest One You’ll Ever See,” opening with any old been-there-done-that monologue is no longer an option. Conan O’Brien was acutely aware of that challenge when he opted to attempt the Movie Awards’ boldest coup yet and score 50 celebrity cameos within the first five minutes of the show.

As you’ve now seen, O’Brien managed to pull off the feat. But he didn’t do it alone. Director Troy Miller tells EW how MTV assembled this “whirlwind of a celebrity-fest” (full list at bottom), which included appearances by Taylor Swift, Ice Cube, Lupita N’yongo, Andy Samberg, Skrillex, Russell Crowe and the Noah cast, Mindy Kaling, Martin Scorsese, the Big Bang Theory gang, Adam Sandler, and even Grumpy Cat.

“It really shows kind of a fun Hollywood community that you don’t normally see unless you’re on a red carpet. It’s the kind of fun you get a sense of [in] the first 10 rows of an awards show,” says Miller, who adds, ”It’s a very cinematic opening.”

According to Miller, the goal of the 2014 MTV Movie Awards opener was to show “Conan using his super powers of writing and acting and getting everyone together to celebrate.” Setting the short to KONGOS’ “Come With Me Now,” Miller says he “really tried to design it directorially as this ongoing story [in which] we follow Conan as he tries to serve the quest of 50 cameos. Each scene triggers the next, it keeps driving forward.”

Miller spent the last three weeks criss-crossing the country and working around O’Brien’s Conan schedule to film and edit dozens of mini-movies that add up to tonight’s final, four-minute cut. Each cameo typically took between five and eight minutes to film, captured thanks to complicated choreography and camerawork assisted by Miller’s Dakota Films crew. ”We would come in with almost military-like precision and literally shoot some of these people in six or seven minutes.” But even that quick turnaround, when multiplied times 50, made for a tremendous amount of footage. ”The biggest hurdle we have all the time is trying to get the run time down because you can wear out your welcome pretty quickly with anything over four or five minutes,” admits Miller.

As for the concept itself, O’Brien, along with Conan writers Mike Sweeney and Michael Gordon, quickly decided to show “Conan going around and catching everybody off-guard. They don’t really want to be in his cameo, but there’s a kind of reluctant acceptance.” That meant tailoring scores of segments to a particular star’s persona or talents. ”The evolution of this really allowed us to have this cool, unusual comic pace. It’s not just the same joke. … He’ll spend some quality time getting a manicure with Taylor Swift, and then the next shot he’s got Chris Pratt in a headlock [and is] forcing him to have a cameo, or he’s walking in on Adam Sandler sitting on the toilet.” The most challenging part, said Miller, was “trying to fine-tune [each bit], like doing Tracy Morgan as Banksy – tell that joke in six seconds.”

Not that Miller isn’t used to the breakneck pace of awards-show productions. Nominated for three Emmys for his work on the Oscars, he got his start with the MTV Movie Awards directing 1993’s nominee parody shorts featuring Brady Bunch cast members. As such, he appreciated a sense of synchronicity and collaboration with O’Briend, a Saturday Night Live writing room alum: “With a guy like Conan, who is not only a great comic actor but is probably one of the top comedy writers in the world, he’s punching [the scene] up while he’s acting it. It’s just the perfect storm with [someone like] Mindy[Kaling].”

Miller continues that even celebrities not typically known for comedy brought plenty to the table. In a segment involving the cast of Noah, Russell Crowe orders costar Emma Watson to “kick [Conan] in the nuts.” That line was actually an improv by Crowe during filming, Miller reveals. In other set-ups, O’Brien tries (and fails) to wow Ice Cube with his beat-boxing skills, then creeps out James Franco by fondling his underwear after Franco finishes performance of Broadway’s Of Mice and Men. “It’s amazing: Being in a play for two and a half hours [and] locking the scene within a few minutes. It’s a big switch. It just shows the capacity [these performers] have to change so quickly and so easily.” He adds, ”It’s a testament to these actors who can get in the sweet spot right away. … That’s the fun about working with some of these pros.”

As for the editing itself, Miller admits, “It’s a total jigsaw puzzle. … For every gag we do, there’s a card on a wall, and we just keep moving them around and say, ‘Hey, does Seth Rogen go well into Sarah Silverman? Let’s make Seth No. 1 and Sarah No. 2.’ Then, after 10, you realize, ‘Hey, we need to go to Taylor because that’s going to be a different pace.’ When you write for a four-minute piece, you look at it like you’re [structuring anything else]: Where are the little breaks? Where does it get predictable? Let’s slow it down… For guys like Conan and his team, they do [this level of work] daily… they know what’s best. There’s not a lot of second-guessing yourself.”